To cancel something because of weather, even if the weather conditions aren't that severe.

Expression originated in a school district just outside Albany, NY called Ichabod Crane Central School District ,which would cancel school for snow, even if there were two flurries, or better yet, even if there was no snow.

Everybody in the Albany area wished they went to Ichabod Crane in the winter.

Well, even though it didn't rain, they went ahead and Ichabod Craned the picnic.

Well, there's a 20% chance of snow, so I guess we'll have to Ichabod Crane the road trip.

During doggy-style anal penetration, smashing a pumpkin over your partner's head at the moment of climax. May result in paralysis or death.

Guy 1: Why is there jack-0-lantern goo all over the living room carpet?
Guy 2: Dude, I was banging the hell out of this chick over the arm of the sofa when I totally ichabod craned her.
Guy 1: Happy Halloween, bee-yotch!